Trifluoroacetic acid → Trifluoroacetic acid

Participants

Reaction Steps

43 mg (0.156 mmol) of (3S)-1-pyrrolo[1,2-a]pyrazin-1-ylpyrrolidin-3-amine dihydrochloride and 33 mg (0.156 mmol) of 6-methylquinazoline-2-carboxylic acid hydrochloride were dissolved in 0.4 mL of NMP. To this mixture was added 85 mg (0.224 mmol) of HATU and 155 μL (0.892 mmol) of N,N-diisopropylethylamine. The mixture was stirred at rt for 30 minutes, then diluted with 3 mL of DMSO and injected directly onto a reverse-phase semi-preparative HPLC system (5-40% acetonitrile/water, 0.1% TFA). Pure fractions were concentrated in vacuo to give 39 mg of the desired product as a TFA salt (51% yield). 1H NMR (400 MHz, CD3OD) δ 9.49 (s, 1 H), 8.04 (d, J=9.1 Hz, 1 H), 7.93 (d, J=6.9 Hz, 2 H), 7.75 (d, J=1.5 Hz, 1 H), 7.70 (d, J=5.9 Hz, 1 H), 7.55 (s, 1 H), 6.92 (s, 1 H), 6.85 (d, J=5.5 Hz, 1 H), 5.00-3.70 (m, 5 H), 3.30 (s, 3 H), 2.60-2.30 (m, 2 H); MS: (ES) m/z calculated for C21H20N6O [M+H]+ 373.2, found 373.

Provenance & Evidence